Formic Acid → HCID 57247295, compound

HRID 965421Notes

Reaction equation

HRID 965421 reaction equation
[F:1][CH2:2][O:3][N:4]=[C:5]([C:9]1[N:13]=[C:12]([NH2:14])[S:11][N:10]=1)[C:6]([NH2:8])=[O:7].[CH:15](O)=[O:16].C(OC(=O)C)(=O)C>>[F:1][CH2:2][O:3][N:4]=[C:5]([C:9]1[N:13]=[C:12]([NH:14][CH:15]=[O:16])[S:11][N:10]=1)[C:6]([NH2:8])=[O:7]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 53935282HCID 53935282, compound

Product 1

HCID 57247295HCID 57247295, compoundYield 61.4%

Procedure

To a suspension of 2-fluoromethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl) acetamide (anti-isomer) (3.51 g, 16 mmol) in 99% formic acid (14.73 g, 320 mmol), acetic anhydride (4.90 g, 48 mmol) was added, and the mixture was reacted at 40° C. for 50 hrs, and then cooled to below 10° C. to separate crystals. The crystals were collected by filtration and washed with cold methanol (10 ml) on Nutsche. The crystals in DMF (16 ml) were heated to dissolve and the resulting solution was dispersed in methanol (32 ml), and then cooled, filtered and dried to give 2-fluoromethoxyimino-2-(5-formamido-1,2,4-thiadiazole-3-yl) acetamide (syn-isomer) (2.43 g, yield: 61.4%). The content obtained by HPLC: 99.0% (anti-isomer: 0.2%).

Workup

  1. additionwas added
  2. customthe mixture was reacted at 40° C. for 50 hrs
  3. temperaturecooled to below 10° C.
  4. customto separate crystals
  5. filtrationThe crystals were collected by filtration
  6. washwashed with cold methanol (10 ml) on Nutsche
  7. temperatureThe crystals in DMF (16 ml) were heated
  8. dissolutionto dissolve
  9. additionthe resulting solution was dispersed in methanol (32 ml)
  10. temperaturecooled
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-2816f18f3d8940e1aac5c54b58b56620
Source dataset
uspto-grants-1998_06
Patent number
US05773624

Reaction notes

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